Identification

Name
Clidinium
Accession Number
DB00771  (APRD00737)
Type
Small Molecule
Groups
Approved
Description

Clidinium is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract. It inhibits muscarinic actions of acetylcholine at postganglionic parasympathetic neuroeffector sites. It is used for the treatment of peptic ulcer disease and also to help relieve abdominal or stomach spasms or cramps due to colicky abdominal pain, diverticulitis, and irritable bowel syndrome.

Structure
Thumb
Synonyms
  • 3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-azonia-bicyclo[2.2.2]octane
  • 3-hydroxy-1-methylquinuclidinium benzilate ester
  • Bromure de Clidinium
  • Bromuro de clidinio
  • Clidinii Bromidum
  • Clidinium bromid
  • N-methyl quinuclidinyl benzilate
Product Ingredients
IngredientUNIICASInChI Key
Clidinium Bromide91ZQW5JF1Z3485-62-9GKEGFOKQMZHVOW-UHFFFAOYSA-M
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ChloraxClidinium Bromide (2.5 mg) + Chlordiazepoxide hydrochloride (5 mg)CapsuleOralAa Pharma Inc1984-12-31Not applicableCanada
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralA-S Medication Solutions2009-09-23Not applicableUs50090 152820180913 8702 1lgynyk
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralOceanside Pharmaceuticals2009-09-23Not applicableUs
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralAvera McKennan Hospital2016-01-18Not applicableUs
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralCameron Pharmaceuticals1966-09-01Not applicableUs
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralCarilion Materials Management2009-09-23Not applicableUs68682 0409 10 nlmimage10 6d39b6cd
Corium CapClidinium Bromide (2.5 mg) + Chlordiazepoxide hydrochloride (5 mg)CapsuleOralIcn Pharmaceuticals1978-12-312005-04-26Canada
LibraxClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralValeant Pharmaceuticals International1966-09-01Not applicableUs
LibraxClidinium Bromide (2.5 mg) + Chlordiazepoxide hydrochloride (5 mg)CapsuleOralValeant Canada Lp Valeant Canada S.E.C.1961-12-31Not applicableCanada
Nu-chlorax Capsules USPClidinium Bromide (2.5 mg) + Chlordiazepoxide hydrochloride (5 mg)CapsuleOralNu Pharm IncNot applicableNot applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Chlordiazepoxide ClidiniumClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralRiver's Edge Pharmaceuticals, LLC2009-06-022012-03-31Us
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralBreckenridge Pharmaceutical, Inc.2009-02-012011-02-28Us
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralMacoven Pharmaceuticals2011-05-042015-06-04Us
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralMarlex Pharmaceuticals Inc2016-07-01Not applicableUs
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralAv Kare, Inc.2013-01-032013-11-04Us
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralBoca Pharmacal, Inc.2009-11-192010-12-20Us
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralEci Pharmaceuticals Llc2011-05-04Not applicableUs
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralAv Kare, Inc.2009-11-192011-12-01Us
Chlordiazepoxide Hydrochloride and Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2016-04-152017-03-24Us
Chlordiazepoxide Hydrochloride And Clidinium BromideClidinium Bromide (2.5 mg/1) + Chlordiazepoxide hydrochloride (5 mg/1)CapsuleOralAcella Pharmaceuticals, LLC2011-08-302016-11-23Us
International/Other Brands
Dolibrax (Roche) / Porsucon (Ying Yuan) / Quarzan (Roche) / Sedaspa (Hua Shin)
Categories
UNII
BO76JF850N
CAS number
7020-55-5
Weight
Average: 352.4467
Monoisotopic: 352.191268703
Chemical Formula
C22H26NO3
InChI Key
HOOSGZJRQIVJSZ-NNBUQUNQSA-N
InChI
InChI=1S/C22H26NO3/c1-23-14-12-17(13-15-23)20(16-23)26-21(24)22(25,18-8-4-2-5-9-18)19-10-6-3-7-11-19/h2-11,17,20,25H,12-16H2,1H3/q+1/t17-,20?,23+
IUPAC Name
(1s,4s)-3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1-methyl-1-azabicyclo[2.2.2]octan-1-ium
SMILES
C[N@@+]12CC[C@@H](CC1)C(C2)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of peptic ulcer disease and also to help relieve abdominal or stomach spasms or cramps due to colicky abdominal pain, diverticulitis, and irritable bowel syndrome.

Associated Conditions
Pharmacodynamics

Clidinium is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract.

Mechanism of action

Inhibits muscarinic actions of acetylcholine at postganglionic parasympathetic neuroeffector sites primarily by inhibiting the M1 muscarinic receptors.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Signs of toxicity include confusion, paralytic ileus, urinary hesitancy/retention, and blurred vision.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe risk or severity of adverse effects can be increased when Clidinium is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
1,10-PhenanthrolineThe therapeutic efficacy of Clidinium can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Clidinium is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Clidinium is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Clidinium is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Clidinium is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Clidinium is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Clidinium is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Clidinium is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Clidinium is combined with Acepromazine.
Food Interactions
Not Available

References

Synthesis Reference

Sternbach, L.H.; US. Patent 2,648,667; August 11,1953; assigned to Hoffmann-LaRoche, Inc.

General References
Not Available
External Links
Human Metabolome Database
HMDB0014909
KEGG Compound
C07853
PubChem Compound
2784
PubChem Substance
46507814
ChemSpider
26330531
BindingDB
50055977
ChEBI
3743
Therapeutic Targets Database
DAP001117
PharmGKB
PA164781044
IUPHAR
366
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Clidinium
ATC Codes
A03CA02 — Clidinium and psycholeptics

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Hoffmann la roche inc
Packagers
  • Avkare Incorporated
  • Boca Pharmacal
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Excellium Pharmaceutical Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • KVK-Tech Inc.
  • Legacy Pharmaceuticals Packaging LLC
  • Macoven Pharmaceuticals LLC
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Oceanside Pharmaceuticals Incorporated
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Provident Pharmaceuticals LLC
  • Resource Optimization and Innovation LLC
  • River's Edge Pharmaceuticals
  • Southwood Pharmaceuticals
  • Veratex Corp.
Dosage forms
FormRouteStrength
CapsuleOral
Prices
Unit descriptionCostUnit
Quarzan 5 mg capsule0.3USD capsule
Quarzan 2.5 mg capsule0.23USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240-241 °CSternbach, L.H.; US. Patent 2,648,667; August 11,1953; assigned to Hoffmann-LaRoche, Inc.
Predicted Properties
PropertyValueSource
Water Solubility0.000377 mg/mLALOGPS
logP-0.5ALOGPS
logP-1.1ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.14 m3·mol-1ChemAxon
Polarizability38.76 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9243
Blood Brain Barrier+0.9142
Caco-2 permeable+0.671
P-glycoprotein substrateSubstrate0.8526
P-glycoprotein inhibitor INon-inhibitor0.7661
P-glycoprotein inhibitor IINon-inhibitor0.9576
Renal organic cation transporterInhibitor0.6314
CYP450 2C9 substrateNon-substrate0.7781
CYP450 2D6 substrateNon-substrate0.6956
CYP450 3A4 substrateSubstrate0.6095
CYP450 1A2 substrateNon-inhibitor0.9528
CYP450 2C9 inhibitorNon-inhibitor0.9459
CYP450 2D6 inhibitorInhibitor0.6154
CYP450 2C19 inhibitorNon-inhibitor0.9577
CYP450 3A4 inhibitorNon-inhibitor0.9504
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9889
Ames testNon AMES toxic0.8557
CarcinogenicityNon-carcinogens0.933
BiodegradationReady biodegradable0.7763
Rat acute toxicity2.4948 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8162
hERG inhibition (predictor II)Non-inhibitor0.6539
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Quinuclidines / Piperidines / Tetraalkylammonium salts / Tertiary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts / Organic oxides
show 5 more
Substituents
Diphenylmethane / Quinuclidine / Piperidine / Quaternary ammonium salt / Tetraalkylammonium salt / Tertiary alcohol / Carboxylic acid ester / Organoheterocyclic compound / Azacycle / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carboxylic ester, organic cation, quaternary ammonium ion (CHEBI:3743)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 16:31